Twitter: From Gawky Teen to Responsible Adult

Being a kid can be a lot of fun, but eventually you have to grow up. It happens to all of us, and technology startups are no exception. Until recently, Twitter seemed more like a cool experiment thrown together by a few guys as a side project than an actual company — probably because that’s exactly what it was. But when you have 175 million users and over $150 million in venture financing (and a $1-billion market value), you have to start getting serious, and for better or worse, that’s exactly what Twitter has been doing. The latest signs of that maturation are the departure of Evan Williams as CEO and the company’s renewed interest in cracking down on things like who can use the word “tweet” and when.

The first of these steps is explored in detail in a New York Times piece published this past weekend, in which Williams is described as a visionary when it comes to product design, but more or less an abject failure when it comes to managing people, and the kinds of difficult financial and structural decisions required of a CEO. Williams himself admits this, saying:

I’ve screwed up in many, many, many ways in terms of managing people and product decisions and business.

It’s a tribute to the Twitter co-founder’s own maturity level that he came to realize this and stepped aside in favor of former chief operating officer Dick Costolo, an experienced startup executive with what most people seem to agree are the necessary chops for such a task. Some of Williams’ maturity may have come as a result of some painful experiences along the way — including some bad blood related to his previous startup, Blogger (which was purchased by Google), and the forcing out of Jack Dorsey, one of Twitter’s co-founders and the original CEO of the company, both of which are described in the NYT piece.

Some of what Twitter has been doing as it matures is structural: expanding its headcount dramatically, fixing its stability issues, redesigning the website, launching official apps for the iPhone and Android, etc. But much of what Costolo has done is also aimed at making Twitter a “real” business: not just a cool service that doesn’t know what it wants to be when it grows up, but a business with revenue (via things like Promoted Tweets) and rules. Flexing its muscles as a business and enforcing those rules has caused some tension with what developers call the Twitter “ecosystem.”

The first eruption of this came earlier this year, after Twitter acquired the Tweetie app for the iPhone and investor Fred Wilson talked about the need to “fill the holes” in the company’s feature set. Many developers took that as an attack on them, and some clearly felt betrayed, since many of these third-party apps had helped promote and build Twitter into what it was. This weekend saw a small flashback to that tension, when Twitter’s rules around the use of the word “tweet” and other trademarks got some attention in the blogosphere and on Twitter itself, much of it negative.

In a nutshell, the company says it wants companies to avoid the use of the word “tweet” in their name if their app or service does things other than access Twitter — a clear shot across the bow of services like Tweetdeck. Although there was a lot of grumbling about these directives, it seems like a natural move for Twitter to make. Investor Chris Sacca noted in a Twitter exchange with Hunch co-founder and angel investor Chris Dixon that Facebook has done the same thing with respect to apps and services (Twitter spokesman Sean Garrett also noted that the majority of these rules have been around since last year).

More than anything else, the reaction to Twitter’s new rules sounded like friends criticizing their former childhood pal because he has started wearing a suit and has gone “all corporate,” and is therefore no fun any more. Twitter isn’t out of adolescence just yet; even Williams describes the company as “a 6-foot-tall sixth grader” with a “lack of maturity, despite size and the perception of outsiders.” But there is no question it is becoming more of a business, as it should. Twitter’s challenge now is to maintain some of that spirit of fun — and the support of its ecosystem — as it grows into adulthood.